tert-Butyl 2-oxopiperidine-1-carboxylate → tert-Butyl 4-(2-(6-bromopyridin-2-yl)hydrazono)piperidine-1-carboxylate

HRID 882013Notes

Reaction equation

HRID 882013 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Br:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][NH2:23])[N:17]=1>CO>[Br:15][C:16]1[N:17]=[C:18]([NH:22][N:23]=[C:11]2[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]2)[CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylateHCID 193925882-Bromo-6-hydrazinopyridine

Product 1

HCID 57514756tert-Butyl 4-(2-(6-bromopyridin-2-yl)hydrazono)piperidine-1-carboxylateYield 99.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-Boc piperidinone (13.8 g, 69.1 mmol) was added to a solution of 2-bromo-6-hydrazinylpyridine (13.0 g, 69.1 mmol) in MeOH (240 mL). The resulting solution was stirred at ambient temperature for 2 h. The solution was concentrated and dried to provide the title compound (25.4 g, 99%) as a white foam: 1H NMR (300 MHz, DMSO-d6) δ 9.97 (s, 1H), 7.49 (overlapping dd, J=7.8 Hz, 1H), 7.03 (d, J=8.4 Hz, 1H), 6.88 (d, J=7.5 Hz, 1H), 3.52-3.38 (m, 4H), 2.59-2.40 (m, 2H overlaps with solvent), 2.38 (t, J=5.7 Hz, 2H), 1.41 (s, 9H); ESI MS m/z 369 [M+H]+.

Workup

  1. concentrationThe solution was concentrated
  2. customdried

Sources & evidence

ORD record
ord-b6ff3b7fb3244a56acab02db9511f538
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

Loading…